KR101833759B1 - Novel spiro type organic compounds - Google Patents

Novel spiro type organic compounds Download PDF

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KR101833759B1
KR101833759B1 KR1020160095685A KR20160095685A KR101833759B1 KR 101833759 B1 KR101833759 B1 KR 101833759B1 KR 1020160095685 A KR1020160095685 A KR 1020160095685A KR 20160095685 A KR20160095685 A KR 20160095685A KR 101833759 B1 KR101833759 B1 KR 101833759B1
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김진우
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Abstract

본 발명은 하기 화학식 1로 표시되는 신규한 유기화합물을 제공하며, 상기 유기화합물은 전자재료용, 정밀화학용, 및 의약용으로 사용될 수 있다. 또한 본 발명은 상기 유기화합물을 포함하여 구성되는 유기전계발광소자를 제공한다:
[ 화학식1 ]

Figure 112016073236473-pat00053
The present invention provides a novel organic compound represented by the following Chemical Formula 1, and the organic compound can be used for electronic materials, fine chemicals, and medicines. The present invention also provides an organic electroluminescent device comprising the above organic compound:
[ Chemical Formula 1 ]
Figure 112016073236473-pat00053

Description

신규한 스파이로 타입의 유기화합물{Novel spiro type organic compounds}Novel spiro type organic compounds < RTI ID = 0.0 >

본 발명은 신규한 유기화합물로서 전자재료, 정밀화학, 의약 등의 용도로 사용될 수 있는 스파이로 타입의 유기화합물에 관한 것이다.The present invention relates to a spiro type organic compound which can be used as a novel organic compound in electronic materials, fine chemicals, medicines and the like.

최근 들어 스파이로 타입 유기화합물은 전자재료 분야에서 많이 사용되고 있다. 그러나, 스파이로 타입 유기화합물이 전자재료 분야에서만 사용되는 것은 아니고, 정밀화학, 의약 등의 용도로도 널리 사용될 수 있다. 이하에서는 전자재료 분야 특히 유기전계발광소자 분야의 사용을 중심으로 종래기술을 기술한다.In recent years, spiro type organic compounds have been widely used in the field of electronic materials. However, the spiro-type organic compound is not only used in the field of electronic materials but also widely used for fine chemicals, medicines and the like. Hereinafter, the prior art will be described focusing on use in the field of electronic materials, particularly in the field of organic electroluminescent devices.

유기전계발광 현상을 이용하는 유기전계발광소자는 통상 양극과 음극 및 이들 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기전계발광소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함할 수 있다. 이러한 유기전계발광소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층으로 주입되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥 상태로 떨어질 때 빛이 나게 된다. 이러한 유기전계발광소자는 자발광, 고휘도, 고효율, 낮은 구동 전압, 넓은 시야각, 높은 콘트라스트, 고속 응답성 등의 특성을 갖는 것으로 알려져 있다.An organic electroluminescent device using an organic electroluminescent phenomenon generally has a structure including an anode and a cathode and an organic layer between them. Here, in order to increase the efficiency and stability of the organic electroluminescent device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, . When a voltage is applied between the two electrodes in the structure of such an organic electroluminescent device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When falling to the ground state, light is emitted. Such an organic electroluminescent device is known to have properties such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

유기전계발광소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하 수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도판트계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도판트를 발광층에 소량 혼합하여, 호스트에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.A material used as an organic material layer in an organic electroluminescent device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural color depending on the luminescent color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The principle is that a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, and the excitons generated in the host are transported to the dopant to emit highly efficient light. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

전술한 유기전계발광소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 한다.In order to sufficiently exhibit the excellent characteristics of the organic electroluminescent device described above, a material constituting the organic material layer in the device such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, Should be preceded.

예컨대, 재료의 열안정성이 떨어질 경우 고온 또는 구동온도에서 재료의 결정화가 이루어져 소자의 수명을 단축시키는 원인이 된다. 대표적인 예로, 다이나프틸안트라센 화합물의 경우 좌우 및 상하 대칭성의 분자구조이기 때문에 소자의 온도가 상승하면서 쉽게 결정화가 발생한다. 최근에는 이러한 결정화를 방지하기 위한 수단으로 스파이로 구조를 도입함으로써 박막안정성을 개선하고 있다. 예를 들어, 미국특허 제 5,840,217호는 스파이로바이플루오렌의 유도체인 스파이로-섹시페닐, 스파이로-DPVBi등의 단분자를 개시하고 있다. 그러나 상기에서 공지된 스파이로 화합물은 내열성은 우수하나 구동전압의 높거나 고효율의 발광을 발휘하지 못하는 단점이 있으며 주로 청색영역 재료로 국한되어 사용되고 있다.For example, when the thermal stability of a material is deteriorated, crystallization of the material occurs at a high temperature or at a driving temperature, thereby shortening the lifetime of the device. As a representative example, in the case of the dinaphthylanthracene compound, the crystallization is easily caused by increasing the temperature of the device because of the molecular structure of left and right and up and down symmetry. In recent years, thin film stability is improved by introducing a spiro structure as a means for preventing such crystallization. For example, U.S. Patent No. 5,840,217 discloses monolayers such as spiro-sexyphenyl, spiro-DPVBi, derivatives of spirobifluorene. However, the spiro compounds known in the art have a disadvantage in that they are excellent in heat resistance but can not exhibit a high driving voltage or high efficiency of light emission, and are mainly used as blue region materials.

그러므로, 유기전계발광소자에 이용되는 유기 물질의 구조를 변화시켜 임의의 발광색을 얻거나, 호스트 도펀트 시스템에 의한 여러 가지의 고효율을 얻는 방법을 이용한 유기전계발광소자들이 제안되고 있으나, 아직 만족스러운 휘도, 특성, 수명 및 내구성 등을 제공하지 못하고 있다. Therefore, organic electroluminescent devices using a method of changing the structure of an organic material used in an organic electroluminescent device to obtain an arbitrary luminescent color or obtaining various high efficiencies by a host dopant system have been proposed. However, , Characteristics, life span and durability.

미국특허 제 5,840,217호U.S. Patent No. 5,840,217

본 발명은 전자재료, 정밀화학, 의약 등의 용도로 사용될 수 있는 신규한 유기화합물을 제공하는 것을 목적으로 한다.It is an object of the present invention to provide a novel organic compound which can be used for electronic materials, fine chemicals, medicines and the like.

또한, 본 발명은 정공주입층물질, 정공수송층물질, 전자차단층 물질 또는 발광층 물질로서 유기전계발광소자에 적용할 수 있으며, 유기전계발광소자에 적용할 경우 구동전압을 낮출 수 있으며, 발광효율, 휘도, 열적안정성, 색순도 및 소자수명을 향상시킬 수 있는 신규한 유기화합물을 제공하는 것을 목적으로 한다.The present invention can be applied to an organic electroluminescent device as a hole injecting layer material, a hole transporting layer material, an electron blocking layer material, or a light emitting layer material. When applied to an organic electroluminescent device, a driving voltage can be lowered, And to provide a novel organic compound capable of improving luminance, thermal stability, color purity, and device life.

또한, 본 발명은 상기 유기화합물을 이용한 유기전계발광소자를 제공하는 것을 목적으로 한다.It is another object of the present invention to provide an organic electroluminescent device using the organic compound.

본 발명은, 하기 화학식 1로 표시되는 신규한 유기화합물을 제공한다.The present invention provides a novel organic compound represented by the following formula (1).

[[ 화학식1Formula 1 ]]

Figure 112016073236473-pat00001
Figure 112016073236473-pat00001

상기 식에서 In the above formula

CYCLO는 탄소 4개 또는 5개로 이루어지는 고리이며, CYCLO is a ring consisting of four or five carbons,

상기 CYCLO가 탄소 4개로 이루어지는 고리인 경우 CYCLO를 형성하는 2개의 페닐기는 결합되어 나프탈렌기를 형성하며,When the CYCLO is a ring having four carbon atoms, two phenyl groups forming CYCLO are bonded to form a naphthalene group,

R1, R2, R3, R4, R5, R6, R7 및 R8은 각각 독립적으로 수소, 중수소, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 또는 탄소수 3 내지 40의 시클로 알킬기이거나,R1, R2, R3, R4, R5, R6, R7 and R8 are each independently hydrogen, deuterium, F, Cl, Br, I , CN, Si (CH 3) 3, B (OH) 2, having 1 to 40 carbon atoms Straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, thioalkyl of 1 to 40 carbon atoms, or cycloalkyl group of 3 to 40 carbon atoms,

F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~60의 방향족 탄화수소기이거나,F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain or branched-chain C 1 -C 40 alkyl, thio C 1 -C 40 alkoxy, C 1 to 40 alkyl carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, dibenzofuranyl, dibenzofuranyl, An aromatic hydrocarbon group having 6 to 60 carbon atoms which is substituted or unsubstituted with at least one member selected from the group consisting of pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl groups,

F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 60의 헤테로 방향족 탄화수소기이거나, F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain or branched-chain C 1 -C 40 alkyl, thio C 1 -C 40 alkoxy, C 1 to 40 alkyl carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, dibenzofuranyl, dibenzofuranyl, At least one element selected from the group consisting of S, O, N and Si, which is substituted or unsubstituted with at least one member selected from the group consisting of pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl and quinolinyl groups Or a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms,

F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 및 탄소수 3 내지 40의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이다.F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain having 1 to 40 carbon atoms or branched chain alkyl, thioalkyl having 1 to 40 carbon atoms alkoxy having 1 to 40, and Anthracenyl, phenanthrenyl, pyrenyl substituted with phenyl, biphenyl, naphthyl, anthracenyl, phenyl group substituted or unsubstituted with at least one member selected from the group consisting of a cycloalkyl group having 3 to 40 carbon atoms, An amino group substituted by at least one member selected from the group consisting of dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups.

상기 유기화합물은 전자재료용, 정밀화학용, 및 의약용으로 사용될 수 있다.The organic compound can be used for electronic materials, fine chemicals, and medicines.

또한, 본 발명은 음극과 양극사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기박막층이 협지되어있는 유기전기발광소자에 있어서, The present invention also provides an organic electroluminescent device having an organic thin film layer sandwiched between a cathode and an anode, the organic thin film layer including one or more layers including at least a light emitting layer,

상기 유기박막층중 적어도 1층 이상이 상기 유기화합물을 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기전기발광소자를 제공한다.Wherein at least one of the organic thin film layers contains the organic compound singly or in combination of two or more.

본 발명에 따른 유기화합물은 전자재료, 정밀화학, 의약 등의 용도로 유용하게 사용될 수 있다. The organic compound according to the present invention can be usefully used for electronic materials, fine chemicals, medicines and the like.

또한, 상기 유기화합물은 정공주입층 물질, 정공수송층 물질, 전자차단층 물질 또는 발광층 물질로서 유기전계발광소자에 적용될 수 있으며, 유기전계발광소자에 적용할 경우 구동전압을 낮추며, 발광효율, 휘도, 열적 안정성, 색순도 및 소자수명을 향상시킨다. The organic compound may be applied to an organic electroluminescent device as a hole injecting layer material, a hole transporting layer material, an electron blocking layer material, or a light emitting layer material. When applied to an organic electroluminescent device, the driving voltage is lowered, Thereby improving thermal stability, color purity, and device life.

또한, 본 발명의 유기화합물을 사용하여 제조되는 유기전계발광소자는 고효율 및 장수명 특성을 갖는다.In addition, the organic electroluminescent device manufactured using the organic compound of the present invention has high efficiency and long life characteristics.

본 발명은, 하기 화학식 1로 표시되는 신규한 유기화합물에 관한 것이다물:The present invention relates to a novel organic compound represented by the following general formula (1)

[[ 화학식1Formula 1 ]]

Figure 112016073236473-pat00002
Figure 112016073236473-pat00002

상기 식에서 In the above formula

CYCLO는 탄소 4개 또는 5개로 이루어지는 고리이며, CYCLO is a ring consisting of four or five carbons,

상기 CYCLO가 탄소 4개로 이루어지는 고리인 경우 CYCLO를 형성하는 2개의 페닐기는 결합되어 나프탈렌기를 형성하며,When the CYCLO is a ring having four carbon atoms, two phenyl groups forming CYCLO are bonded to form a naphthalene group,

R1, R2, R3, R4, R5, R6, R7 및 R8은 각각 독립적으로 수소, 중수소, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 또는 탄소수 3 내지 40의 시클로 알킬기이거나,R1, R2, R3, R4, R5, R6, R7 and R8 are each independently hydrogen, deuterium, F, Cl, Br, I , CN, Si (CH 3) 3, B (OH) 2, having 1 to 40 carbon atoms Straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, thioalkyl of 1 to 40 carbon atoms, or cycloalkyl group of 3 to 40 carbon atoms,

F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~60의 방향족 탄화수소기이거나,F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain or branched-chain C 1 -C 40 alkyl, thio C 1 -C 40 alkoxy, C 1 to 40 alkyl carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, dibenzofuranyl, dibenzofuranyl, An aromatic hydrocarbon group having 6 to 60 carbon atoms which is substituted or unsubstituted with at least one member selected from the group consisting of pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl groups,

F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 60의 헤테로 방향족 탄화수소기이거나, F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain or branched-chain C 1 -C 40 alkyl, thio C 1 -C 40 alkoxy, C 1 to 40 alkyl carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, dibenzofuranyl, dibenzofuranyl, At least one element selected from the group consisting of S, O, N and Si, which is substituted or unsubstituted with at least one member selected from the group consisting of pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl and quinolinyl groups Or a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms,

F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 및 탄소수 3 내지 40의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이다.F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain having 1 to 40 carbon atoms or branched chain alkyl, thioalkyl having 1 to 40 carbon atoms alkoxy having 1 to 40, and Anthracenyl, phenanthrenyl, pyrenyl substituted with phenyl, biphenyl, naphthyl, anthracenyl, phenyl group substituted or unsubstituted with at least one member selected from the group consisting of a cycloalkyl group having 3 to 40 carbon atoms, An amino group substituted by at least one member selected from the group consisting of dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups.

바람직하게는 상기 화학식 1은 하기 화학식 2 또는 화학식 3으로 표시될 수 도 있다:Preferably, the formula (1) may be represented by the following formula (2) or (3)

[[ 화학식2(2) ]]

Figure 112016073236473-pat00003
Figure 112016073236473-pat00003

[[ 화학식3(3) ]]

Figure 112016073236473-pat00004
Figure 112016073236473-pat00004

상기 식에서 In the above formula

R1, R2, R3, R4, R5, R6, R7 및 R8은 각각 독립적으로 수소, 중수소, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 또는 탄소수 3 내지 40의 시클로 알킬기이거나,R1, R2, R3, R4, R5, R6, R7 and R8 are each independently hydrogen, deuterium, F, Cl, Br, I , CN, Si (CH 3) 3, B (OH) 2, having 1 to 40 carbon atoms Straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, thioalkyl of 1 to 40 carbon atoms, or cycloalkyl group of 3 to 40 carbon atoms,

F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~60의 방향족 탄화수소기이거나,F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain or branched-chain C 1 -C 40 alkyl, thio C 1 -C 40 alkoxy, C 1 to 40 alkyl carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, dibenzofuranyl, dibenzofuranyl, An aromatic hydrocarbon group having 6 to 60 carbon atoms which is substituted or unsubstituted with at least one member selected from the group consisting of pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl groups,

F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 60의 헤테로 방향족 탄화수소기이거나, F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain or branched-chain C 1 -C 40 alkyl, thio C 1 -C 40 alkoxy, C 1 to 40 alkyl carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, dibenzofuranyl, dibenzofuranyl, At least one element selected from the group consisting of S, O, N and Si, which is substituted or unsubstituted with at least one member selected from the group consisting of pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl and quinolinyl groups Or a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms,

F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 및 탄소수 3 내지 40의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이다.F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain having 1 to 40 carbon atoms or branched chain alkyl, thioalkyl having 1 to 40 carbon atoms alkoxy having 1 to 40, and Anthracenyl, phenanthrenyl, pyrenyl substituted with phenyl, biphenyl, naphthyl, anthracenyl, phenyl group substituted or unsubstituted with at least one member selected from the group consisting of a cycloalkyl group having 3 to 40 carbon atoms, An amino group substituted by at least one member selected from the group consisting of dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups.

더욱 바람직하게는 상기 식에서,More preferably, in the above formula,

R1, R2, R3, R4, R5, R6, R7 및 R8은 각각 독립적으로 수소, 중수소, F, Cl, Br, I, B(OH)2, 또는 탄소수 1 내지 10의 직쇄 또는 분지쇄 알킬기이거나,Wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7 and R 8 are each independently selected from the group consisting of hydrogen, deuterium, F, Cl, Br, I, B (OH) 2 or a straight or branched alkyl group having 1 to 10 carbon atoms,

F, Cl, Br, I, B(OH)2, 및 탄소수 1 내지 10의 직쇄 또는 분지쇄 알킬기, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 페난트렌일, 파이레닐기이거나,(I) wherein R 1 and R 2 are each independently selected from the group consisting of F, Cl, Br, I, B (OH) 2 and straight or branched chain alkyl groups having 1 to 10 carbon atoms, anthracenyl, phenanthrenyl, pyrenyl substituted with phenyl, biphenyl, naphthyl, anthracenyl, , Pyridyl, pyridinyl, pyrimidinyl, quinolinyl, and quinolinyl groups, each of which is optionally substituted with one or more substituents selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, A substituted or unsubstituted phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl,

F, Cl, Br, I, B(OH)2, 및 탄소수 1 내지 10의 직쇄 또는 분지쇄 알킬기, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 퀴놀리닐기, 9,9-디메틸플루오레닐, 카르바졸일, 또는 디벤조퓨란일기이거나,(I) wherein R 1 and R 2 are each independently selected from the group consisting of F, Cl, Br, I, B (OH) 2 and straight or branched chain alkyl groups having 1 to 10 carbon atoms, anthracenyl, phenanthrenyl, pyrenyl substituted with phenyl, biphenyl, naphthyl, anthracenyl, Substituted or unsubstituted pyrroles selected from the group consisting of pyrrolidinyl, pyrrolidinyl, pyrrolidinyl, pyrrolidinyl, pyrrolidinyl, pyrrolidinyl, pyrrolidinyl, Triazol, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, 9,9-dimethylfluorenyl, carbazolyl, or dibenzofuranyl group,

F, Cl, Br, I, B(OH)2, 및 탄소수 1 내지 10의 직쇄 또는 분지쇄 알킬기, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 및 디벤조퓨란일기로 이루어진 군으로부터 선택되는 하나 이상으로 치환된 아미노기일 수 있다.(I) wherein R 1 and R 2 are each independently selected from the group consisting of F, Cl, Br, I, B (OH) 2 and straight or branched chain alkyl groups having 1 to 10 carbon atoms, anthracenyl, phenanthrenyl, pyrenyl substituted with phenyl, biphenyl, naphthyl, anthracenyl, , 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, and dibenzofuranyl groups.

상기 화학식 2 또는 화학식 3으로 표시되는 화합물의 구체적인 예를 들면 하기 화학식 1 내지 48일 수 있다.Specific examples of the compound represented by Formula 2 or Formula 3 include the following Formula 1 to Formula 48.

Figure 112016073236473-pat00005
Figure 112016073236473-pat00005

Figure 112016073236473-pat00006
Figure 112016073236473-pat00006

Figure 112016073236473-pat00007
Figure 112016073236473-pat00007

Figure 112016073236473-pat00008
Figure 112016073236473-pat00008

Figure 112016073236473-pat00009
Figure 112016073236473-pat00009

Figure 112016073236473-pat00010
Figure 112016073236473-pat00010

Figure 112016073236473-pat00011
Figure 112016073236473-pat00011

Figure 112016073236473-pat00012
Figure 112016073236473-pat00012

Figure 112016073236473-pat00013
Figure 112016073236473-pat00013

Figure 112016073236473-pat00014
Figure 112016073236473-pat00014

Figure 112016073236473-pat00015
Figure 112016073236473-pat00015

Figure 112016073236473-pat00016
Figure 112016073236473-pat00016

Figure 112016073236473-pat00017
Figure 112016073236473-pat00017

본 발명의 유기화합물은 전자재료용, 정밀화학용, 의약용 등으로 사용될 수 있다.The organic compound of the present invention can be used for electronic materials, fine chemicals, medicines and the like.

상기 화합물들은 최종 화합물뿐만 아니라, 다른 화합물을 합성하기 위한 중간체로서 사용될 수도 있다.These compounds may be used as an intermediate for synthesizing not only the final compound but also other compounds.

상기 유기화합물은 유기전계발광소자용 재료 중 정공주입층 물질, 정공수송층 물질, 전자차단층 물질, 발광층 물질, 전자수송층 물질 또는 전자주입층 물질로 사용될 수 있다.The organic compound may be used as a hole injecting layer material, a hole transporting layer material, an electron blocking layer material, a light emitting layer material, an electron transporting layer material, or an electron injection layer material in the material for an organic electroluminescence device.

또한, 본 발명은In addition,

음극과 양극사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기박막층이 협지되어있는 유기전기발광소자에 있어서, An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,

상기 유기박막층중 적어도 1층 이상이 상기 유기화합물을 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기전기발광소자에 관한 것이다.Wherein at least one of the organic thin film layers contains the organic compound singly or in combination of two or more kinds.

상기 유기전기발광소자는 양극, 정공주입층, 정공수송층, 전자차단층, 발광층, 전자수송층, 전자주입층 및 음극이 이 순서대로 적층된 구조를 가질 수 있다.The organic electroluminescent device may have a structure in which an anode, a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode are stacked in this order.

이하에서, 본 발명의 유기전계발광소자에 대하여 예를 들어 설명한다. 그러나, 하기에 예시된 내용이 본 발명의 유기전계발광소자를 한정하는 것은 아니다. 하기 유기전계발광소자에서 상기 유기화합물은 정공주입층 물질, 정공수송층 물질, 전자차단층 물질, 발광층 물질, 전자수송층 물질 또는 전자주입층 물질로 사용될 수 있다. Hereinafter, the organic electroluminescent device of the present invention will be described by way of example. However, the following examples do not limit the organic electroluminescent device of the present invention. In the following organic electroluminescent device, the organic compound may be used as a hole injecting layer material, a hole transporting layer material, an electron blocking layer material, a light emitting layer material, an electron transporting layer material, or an electron injection layer material.

본 발명에 따른 유기 전계발광 소자의 제조방법으로는, 먼저 기판표면에 양극용 물질을 통상적인 방법으로 코팅하여 양극을 형성한다. 이때, 사용되는 기판은 투명성, 표면평활성, 취급용이성 및 방수성이 우수한 유리기판 또는 투명플라스틱기판이 바람직하다. 또한, 양극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등이 사용될 수 있다.In the method of manufacturing an organic electroluminescent device according to the present invention, a cathode material is coated on the surface of a substrate by a conventional method to form a cathode. At this time, the substrate to be used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness. As the material for the positive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity may be used.

다음으로, 상기 양극표면에 정공주입층(HIL) 물질을 통상적인 방법으로 진공열증착 또는 스핀코팅하여 정공주입층을 형성한다. 이러한 정공주입층 물질로는 구리프탈로시아닌(CuPc), 4,4',4"-트리스(3-메틸페닐아미노)트리페닐아민(m-MTDATA), 4,4',4"-트리스(3-메틸페닐아미노)페녹시벤젠(m-MTDAPB), 스타버스트(starburst)형아민류인 4,4',4"-트리(N-카바졸릴)트리페닐아민(TCTA), 4,4',4"-트리스(N-(2-나프틸)-N-페닐아미노)-트리페닐아민(2-TNATA) 또는 이데미츠사(Idemitsu)에서 구입가능한 IDE406을 예로 들 수 있다.Next, a hole injection layer (HIL) material is formed on the surface of the anode by vacuum thermal deposition or spin coating using a conventional method. Examples of such hole injection layer materials include copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4,4' Amino) phenoxybenzene (m-MTDAPB), starburst type amines such as 4,4 ', 4 "-tri (N-carbazolyl) triphenylamine (TCTA), 4,4' Triphenylamine (2-TNATA) or IDE406 available from Idemitsu, for example.

상기 정공주입층 표면에 정공수송층(HTL) 물질을 통상적인 방법으로 진공열증착 또는 스핀코팅하여 정공수송층을 형성한다. 이때, 정공수송층 물질로는 비스(N-(1-나프틸-n-페닐))벤지딘(α-NPD), N,N'-다이(나프탈렌-1-일)-N,N'-바이페닐-벤지딘(NPB) 또는 N,N'-바이페닐-N,N'-비스(3-메틸페닐)-1,1'-바이페닐-4,4'-다이아민(TPD)을 예로 들 수 있다. A hole transport layer (HTL) material is vacuum-deposited or spin coated on the surface of the hole injection layer by a conventional method to form a hole transport layer. In this case, the hole transport layer material may be at least one selected from the group consisting of bis (N- (1-naphthyl-n-phenyl)) benzidine (? -NPD), N, -Benzidine (NPB) or N, N'-biphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine (TPD).

상기 정공수송층 표면에 발광층(EML) 물질을 통상적인 방법으로 진공열증착 또는 스핀코팅하여 발광층을 형성한다. 이때, 사용되는 발광 재료로서 예를 들면 축광 형광재료, 형광증백제, 레이저 색소, 유기 신틸레이터 및 형광 분석용 시약을 들 수 있다. 구체적으로는, 카바졸계 화합물, 포스핀옥사이드계 화합물, 카바졸계 포스핀옥사이드 화합물, 비스((3,5-디플루오로-4-시아노페닐)피리딘) 이리듐 피콜리네이트(FCNIrpic), 트리스(8-히드록시퀴놀린) 알루미늄(Alq3), 안트라센, 페난트렌, 피렌, 크리센, 페릴렌, 코로넨, 루브렌 및 퀴나크리돈과 같은 폴리아로마틱 화합물, 퀴터페닐과 같은 올리고페닐렌 화합물, 1,4-비스 (2-메틸스티릴)벤젠, 1,4-비스(4-메틸스티릴)벤젠, 1,4-비스(4-메틸-5-페닐-2-옥사졸릴)벤젠, 1,4-비스(5-페닐-2-옥사졸릴)벤젠, 2,5-비스(5-t-부틸-2-벤즈옥사졸릴)사이오펜, 1,4-바이페닐-1,3-부타디엔, 1,6-바이페닐-1,3,5-헥사트리엔, 1,1,4,4-테트라페닐-1,3-부타디엔과 같은 액체신틸레이션용 신틸레이터, 옥신유도체의 금속착체, 쿠마린 색소, 디시아노메틸렌피란 색소, 디시아노메틸렌사이오피란 색소, 폴리메틴 색소, 옥소벤즈안트라센 색소, 크산텐 색소, 카르보스티릴 색소, 페릴렌 색소, 옥사진 화합물, 스틸벤 유도체, 스피로 화합물, 옥사디아졸 화합물 등을 들 수 있다. A light emitting layer (EML) material is formed on the surface of the hole transport layer by vacuum thermal deposition or spin coating using a conventional method. Examples of the light-emitting material to be used herein include a phosphorescent fluorescent material, a fluorescent whitening agent, a laser dye, an organic scintillator, and a reagent for fluorescence analysis. Specifically, there may be mentioned a carbazole-based compound, a phosphine oxide-based compound, a carbazole-based phosphine oxide compound, bis ((3,5-difluoro-4-cyanophenyl) pyridine) iridium picolinate (FCNIrpic) 8-hydroxyquinoline) Polyaromatic compounds such as aluminum (Alq3), anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds such as quaterphenyl, Benzene, 1,4-bis (4-methylstyryl) benzene, 1,4-bis (4-methylstyryl) Bis (5-t-butyl-2-benzoxazolyl) thiophene, 1,4-biphenyl-1,3-butadiene, Liquid scintillation scintillators such as 6-biphenyl-1,3,5-hexatriene and 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of oxine derivatives, coumarin dyes, Methylene pyran pigment, dicyanomethylene cyopyran pigment, poly A thiophene dye, a pyridine dye, an oxazine compound, a stilbene derivative, a spiro compound, an oxadiazole compound, and the like.

선택적으로는, 정공수송층과 발광층사이에 전자차단층(EBL)을 추가로 형성할 수 있다. Alternatively, an electron blocking layer (EBL) may be additionally formed between the hole transporting layer and the light emitting layer.

상기 발광층표면에 전자수송층(ETL) 물질을 통상적인 방법으로 진공열증착 또는 스핀코팅하여 전자수송층을 형성한다. 이때, 사용되는 전자수송층 물질의 경우 특별히 제한되지 않으며, 바람직하게는 트리스(8-하이드록시퀴놀리놀라토)알루미늄(Alq3)을 사용할 수 있다. 또한, 본 발명의 유기화합물도 바람직하게 사용될 수 있다.An electron transport layer (ETL) material is formed on the surface of the light emitting layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the electron transporting material to be used is not particularly limited, and tris (8-hydroxyquinolinolato) aluminum (Alq 3 ) can be preferably used. Also, the organic compound of the present invention can be preferably used.

선택적으로는, 발광층과 전자수송층사이에 정공차단층(HBL)을 추가로 형성하고 발광층에 인광도펀트를 함께 사용함으로써, 삼중항여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지할 수 있다. Alternatively, by further forming a hole blocking layer (HBL) between the light emitting layer and the electron transporting layer and using a phosphorescent dopant together with the light emitting layer, it is possible to prevent the phenomenon that the triplet excitons or holes are diffused into the electron transporting layer.

정공차단층의 형성은 정공차단층물질을 통상적인 방법으로 진공열증착 및 스핀코팅하여 실시할 수 있으며, 정공차단층 물질의 경우 특별히 제한되지는 않으나, 바람직하게는 (8-하이드록시퀴놀리놀라토)리튬(Liq), 비스(8-하이드록시-2-메틸퀴놀리놀나토)-알루미늄비페녹사이드(BAlq), 바쏘쿠프로인 (bathocuproine, BCP) 및 LiF 등을 사용할 수 있다.The hole blocking layer can be formed by vacuum thermal deposition and spin coating using a hole blocking layer material in a conventional manner. In the case of the hole blocking layer material, there is no particular limitation, but (8-hydroxyquinolinolato Lithium biphenoxide (BAlq), bathocuproine (BCP), LiF, etc. may be used as the lithium salt (Li), bis (8-hydroxy-2-methylquinolinonato)

상기 전자수송층 표면에 전자주입층(EIL) 물질을 통상적인 방법으로 진공열증착 또는 스핀코팅하여 전자주입층을 형성한다. 이때, 사용되는 전자주입층 물질로는 LiF, Liq, Li2O, BaO, NaCl, CsF 등의 물질이 사용될 수 있다.An electron injection layer (EIL) material is formed on the surface of the electron transport layer by vacuum thermal deposition or spin coating using a conventional method. At this time, as the electron injection layer material to be used may be a material such as LiF, Liq, Li 2 O, BaO, NaCl, CsF.

상기 전자주입층표면에 음극용물질을 통상적인 방법으로 진공열증착하여 음극을 형성한다.A negative electrode is formed on the surface of the electron injecting layer by vacuum thermal deposition using a conventional method.

이때, 사용되는 음극용물질로는 리튬(Li), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘(Mg), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등이 사용될 수 있다. 또한, 전면발광유기 전계발광 소자의 경우 산화인듐주석(ITO) 또는 산화인듐아연(IZO)를 사용하여 빛이 투과할 수 있는 투명한 음극을 형성할 수도 있다.At this time, as the negative electrode material to be used, lithium, aluminum, aluminum-lithium, calcium, magnesium, (Mg-Ag) or the like may be used. In the case of a top emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode which can transmit light.

상기 음극의 표면에는 본 발명의 캡핑층 형성용 조성물에 의해 캡핑층(CPL)이 형성될 수 있다.A capping layer (CPL) may be formed on the surface of the cathode by the composition for forming a capping layer of the present invention.

본 발명에 따른 유기전계발광소자는 상술한 바와 같은 순서, 즉 양극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/음극 순으로 제조하여도 되고, 그 반대로 음극/전자주입층/전자수송층/발광층/정공수송층/정공주입층/양극 순서로 제조하여도 무방하다.The organic electroluminescent device according to the present invention may be manufactured in the order as described above, that is, in the order of anode / hole injecting layer / hole transporting layer / light emitting layer / electron transporting layer / electron injecting layer / cathode, Electron transporting layer / light emitting layer / hole transporting layer / hole injecting layer / anode.

이하에서, 상기 화학식 1의 화합물의 합성방법을 대표적인 예를 들어 하기에 설명한다. 그러나, 본 발명의 화합물들의 합성방법이 하기 예시된 방법으로 한정되는 것은 아니며, 본 발명의 화합물들은 하기에 예시된 방법과 이 분야의 공지의 방법에 의해 제조될 수 있다.Hereinafter, a method of synthesizing the compound of Formula 1 will be described with reference to typical examples. However, the method of synthesizing the compounds of the present invention is not limited to the following exemplified methods, and the compounds of the present invention can be produced by the methods exemplified below and by methods known in the art.

중간체 1의 합성Synthesis of Intermediate 1

[반응식 1][Reaction Scheme 1]

Figure 112016073236473-pat00018
Figure 112016073236473-pat00018

질소 하에서 나프토산 1.72g(10mmol)을 10 ml의 THF 중에 용해시키고, -40℃에서 1.4M sec-BuLi 10ml와 혼합한다. 냉각 조를 제거하고 반응 용액을 대략 30분 내에 수조 내에서 실온이 되도록 방치하고, 추가로 2시간 동안 교반하였다. 그 후, 그것을 -78℃로 냉각시키고, 메탄설폰산 1.44g(15mmol)이 섞인 THF 10ml를 적가한다. 냉각조를 제거하고, 혼합물을 대략 30분 내에 수조 내에서 실온이 되도록 방치하고, 60℃에서 2시간 동안 환류시킨다.Under nitrogen, 1.72 g (10 mmol) of naphthoic acid are dissolved in 10 ml of THF and mixed with 10 ml of 1.4 M sec-BuLi at -40 ° C. The cooling bath was removed and the reaction solution was allowed to stand at room temperature within approximately 30 minutes in the water bath and stirred for an additional 2 hours. It is then cooled to -78 ° C and 10 ml of THF in which 1.44 g (15 mmol) of methanesulfonic acid is added is added dropwise. The cooling bath is removed and the mixture is allowed to stand at room temperature in the water bath within approximately 30 minutes and refluxed at 60 DEG C for 2 hours.

반응이 종료되면 포화 염화나트륨 용액으로 씻어주고 2N-HCl 수용액을 넣고, 30분간 교반시킨 후 에테르로 추출하였다.After completion of the reaction, the reaction mixture was washed with a saturated sodium chloride solution, and an aqueous 2N-HCl solution was added thereto. The reaction mixture was stirred for 30 minutes and then extracted with ether.

무수 MgSO4로 유기층 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 화합물을 Hex : EA = 5 : 1로 컬럼하여 화합물-1 0.79g(51%)을 얻었다.Water in the organic layer was removed with anhydrous MgSO 4, filtered under reduced pressure, and the organic solvent was concentrated. The resulting compound was subjected to column chromatography with Hex: EA = 5: 1 to obtain 0.79 g (51%) of Compound-1.

중간체 1 MS(FAB): 154(M+)Intermediate 1 MS (FAB): 154 (M <+> )

화합물 1의 합성Synthesis of Compound 1

[반응식 2][Reaction Scheme 2]

Figure 112016073236473-pat00019
Figure 112016073236473-pat00019

1-브로모-4-요오도나프탈렌 3.33g(10mmol)을 THF 15ml에 녹인 후 -78℃로 낮추고 2.5M n-BuLi 4ml를 적가하였다. -78℃에서 1시간 교반 후 THF 30ml에 녹인 중간체 1 1.54g(10mmol)을 천천히 적가하고 상온으로 승온하여 반응을 완결한 후 MC와 2N HCl을 첨가하고 유기층을 추출하였다.3.33 g (10 mmol) of 1-bromo-4-iodonaphthalene was dissolved in 15 ml of THF, then cooled to -78 ° C, and 4 ml of 2.5 M n-BuLi was added dropwise. After stirring at -78 ° C for 1 hour, 1.54 g (10 mmol) of Intermediate 1 dissolved in 30 ml of THF was slowly added dropwise and the temperature was raised to room temperature to complete the reaction. MC and 2N HCl were added and the organic layer was extracted.

무수 MgSO4로 유기층 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 화합물을 Hex : EA = 5 : 1로 컬럼하여 화합물-2 2.76g(76%)을 얻었다.Water in the organic layer was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting compound was subjected to column chromatography with Hex: EA = 5: 1 to obtain 2.76 g (76%) of Compound-

상기 중간체 2를 아세트산에 녹인 후 진한 염산을 첨가하고 1시간 환류하여 반응을 완결하였다. 에테르와 물을 사용하여 추출한 후 유기층을 포화된 NaHCO3으로 씻어주었다. 유기층을 MgSO4로 건조한 후 재결정 및 Hex : EA = 4 : 1로 컬럼하여 화합물 1 2.85g(83%)을 얻었다.The intermediate 2 was dissolved in acetic acid, concentrated hydrochloric acid was added, and the mixture was refluxed for 1 hour to complete the reaction. After extracting with ether and water, the organic layer was washed with saturated NaHCO 3 . The organic layer was dried over MgSO 4 , recrystallized, and then subjected to column chromatography with Hex: EA = 4: 1 to obtain 2.85 g (83%) of Compound 1.

중간체 2 MS(FAB): 363(M+)Intermediate 2 MS (FAB): 363 (M <+> )

화합물 1 MS(FAB): 343(M+)Compound 1 MS (FAB): 343 (M <+> )

화합물 2의 합성Synthesis of Compound 2

[반응식 3][Reaction Scheme 3]

Figure 112016073236473-pat00020
Figure 112016073236473-pat00020

3-브로모-1-요오도나프탈렌 3.33g(10mmol)을 THF 15ml에 녹인 후 -78℃로 낮추고 2.5M n-BuLi 4ml를 적가하였다. -78℃에서 1시간 교반 후 THF 30ml에 녹인 중간체 1 1.54g(10mmol)을 천천히 적가하고 상온으로 승온하여 반응을 완결한 후 MC와 2N HCl을 첨가하고 유기층을 추출하였다.3.33 g (10 mmol) of 3-bromo-1-iodonaphthalene was dissolved in 15 ml of THF, then cooled to -78 ° C, and 4 ml of 2.5 M n-BuLi was added dropwise. After stirring at -78 ° C for 1 hour, 1.54 g (10 mmol) of Intermediate 1 dissolved in 30 ml of THF was slowly added dropwise and the temperature was raised to room temperature to complete the reaction. MC and 2N HCl were added and the organic layer was extracted.

무수 MgSO4로 유기층 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 화합물을 Hex : EA = 5 : 1로 컬럼하여 중간체 3 2.72g(75%)을 얻었다.Water in the organic layer was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting compound was subjected to column chromatography with Hex: EA = 5: 1 to obtain 2.72 g (75%) of Intermediate 3.

상기 화합물-3를 아세트산에 녹인 후 진한 염산을 첨가하고 1시간 환류하여 반응을 완결하였다. 에테르와 물을 사용하여 추출한 후 유기층을 포화된 NaHCO3으로 씻어주었다. 유기층을 MgSO4로 건조한 후 재결정 및 Hex : EA = 4 : 1로 컬럼하여 화합물 2 2.75g(80%)을 얻었다.The compound-3 was dissolved in acetic acid, concentrated hydrochloric acid was added, and the reaction was completed by refluxing for 1 hour. After extracting with ether and water, the organic layer was washed with saturated NaHCO 3 . The organic layer was dried over MgSO 4 , recrystallized and columned with Hex: EA = 4: 1 to obtain 2.75 g (80%) of Compound 2. [

중간체 3 MS(FAB): 363(M+)Intermediate 3 MS (FAB): 363 (M &lt; + & gt ; ) [

화합물 2 MS(FAB): 343(M+)Compound 2 MS (FAB): 343 (M &lt; + & gt ; ).

화합물 3의 합성Synthesis of Compound 3

[반응식 4][Reaction Scheme 4]

Figure 112016073236473-pat00021
Figure 112016073236473-pat00021

질소 하에서 화합물 1 3.43g(10mmol)을 무수 THF 40ml에 녹이고, 반응물의 온도를 -78℃로 낮추고, 2.5M n-BuLi 4ml를 천천히 적가하고 난 후, 반응물을 0℃에서 1시간동안 교반시켰다. 이후, 반응물의 온도를 -78℃로 낮추고 트리메틸보레이트 12.47g(12mmol)을 적가하고 난 후 상온에서 12시간동안 교반시켰다. 반응이 종결되면 2N-HCl 수용액을 넣고, 30분간 교반시킨 후 에테르로 추출하였다.Under nitrogen, 3.43 g (10 mmol) of Compound 1 was dissolved in 40 ml of anhydrous THF, the temperature of the reaction was lowered to -78 ° C, 4 ml of 2.5 M n-BuLi was slowly added dropwise and the reaction was stirred at 0 ° C for 1 hour. Then, the temperature of the reactant was lowered to -78 ° C, 12.47 g (12 mmol) of trimethylborate was added dropwise, and the mixture was stirred at room temperature for 12 hours. When the reaction was completed, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether.

무수 MgSO4로 유기층 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 화합물을 Hex : EA = 5 : 1로 컬럼하여 화합물 3 2.43g(79%)을 얻었다.Water in the organic layer was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting compound was subjected to column chromatography with Hex: EA = 5: 1 to obtain 2.43 g (79%) of Compound 3.

화합물 3 MS(FAB): 334(M+)Compound 3 MS (FAB): 334 (M <+> ) <

화합물 4의 합성Synthesis of Compound 4

[반응식 5][Reaction Scheme 5]

Figure 112016073236473-pat00022
Figure 112016073236473-pat00022

질소 하에서 화합물 3 3.08g(10mmol)과 1-브로모-3-요오도벤젠 2.83g(10mmol)을 주입하고 THF 40ml에 녹인 후, Pd(PPh3)4 0.58g(0.5mmol)과 2M K2CO3 15ml(30mmol)를 각각 넣은 다음 24시간 동안 환류시켰다.After three nitrogen compound 3.08g (10mmol) and 1-bromo-3-iodo-benzene injection 2.83g (10mmol) is dissolved in THF 40ml, Pd (PPh 3) 4 0.58g (0.5mmol) and 2M K 2 15 ml (30 mmol) of CO 3 were added, respectively, and the mixture was refluxed for 24 hours.

반응이 종료되면 반응물의 온도를 상온으로 식히고, MC 200ml, H2O 200ml를 첨가하여 MC층을 추출한 후 무수 MgSO4로 건조하고 농축한 후 Hex : EA = 5 : 1로 컬럼하여 화합물 4 2.97g(71%)을 얻었다.After completion of the reaction, the reaction mixture was cooled to room temperature, and 200 ml of MC and 200 ml of H 2 O were added thereto. The MC layer was extracted, dried over anhydrous MgSO 4 and concentrated. The product was then subjected to column chromatography with Hex: EA = 5: (71%).

1H NMR (DMSO, 300Hz): δ(ppm)= 8.22-7.66 (m, 4H), 7.64-7.23(m, 7H), 7.20-6.70(d, 4H) 1 H NMR (DMSO, 300 Hz):? (Ppm) = 8.22-7.66 (m, 4H), 7.64-7.23 (m, 7H), 7.20-6.70

화합물 4 MS(FAB): 419(M+)Compound 4 MS (FAB): 419 (M &lt; + & gt ; ).

화합물 5의 합성Synthesis of Compound 5

[반응식 6][Reaction Scheme 6]

Figure 112016073236473-pat00023
Figure 112016073236473-pat00023

질소 하에서 화합물 3 3.08g(10mmol)과 1-브로모-4-요오도벤젠 2.83g(10mmol)을 주입하고 THF 40ml에 녹인 후, Pd(PPh3)4 0.58g(0.5mmol)과 2M K2CO3 15ml(30mmol)를 각각 넣은 다음 24시간 동안 환류시켰다.After three nitrogen compound 3.08g (10mmol) and 1-bromo-4-iodo benzene injection 2.83g (10mmol) is dissolved in THF 40ml, Pd (PPh 3) 4 0.58g (0.5mmol) and 2M K 2 15 ml (30 mmol) of CO 3 were added, respectively, and the mixture was refluxed for 24 hours.

반응이 종료되면 반응물의 온도를 상온으로 식히고, MC 200ml, H2O 200ml를 첨가하여 MC층을 추출한 후 무수 MgSO4로 건조하고 농축한 후 Hex : EA = 4 : 1로 컬럼하여 화합물 5 2.89g(69%)을 얻었다.After the completion of the reaction, the reaction mixture was cooled to room temperature, 200 ml of MC and 200 ml of H 2 O were added to extract the MC layer. The mixture was dried over anhydrous MgSO 4 and concentrated. The product was then subjected to column chromatography with Hex: EA = 4: (69%).

1H NMR (DMSO, 300Hz): δ(ppm)= 8.22-7.66 (m, 4H), 7.64-7.26(m, 7H), 7.22-6.70(d, 4H) 1 H NMR (DMSO, 300 Hz):? (Ppm) = 8.22-7.66 (m, 4H), 7.64-7.26

화합물 5 MS(FAB): 419(M+)Compound 5 MS (FAB): 419 (M &lt; + & gt ; ).

화합물 6의 합성Synthesis of Compound 6

[반응식 7][Reaction Scheme 7]

Figure 112016073236473-pat00024
Figure 112016073236473-pat00024

1-요오도나프탈렌 2.54g(10mmol)을 THF 15ml에 녹인 후 -78℃로 낮추고 2.5M n-BuLi 4ml를 적가하였다. -78℃에서 1시간 교반 후 THF 30ml에 녹인 2-브로모-9H-플루오렌-9-온 2.59g(10mmol)을 천천히 적가하고 상온으로 승온하여 반응을 완결한 후 MC와 2N HCl을 첨가하고 유기층을 추출하였다.2.54 g (10 mmol) of 1-iodonaphthalene was dissolved in 15 ml of THF and then cooled to -78 ° C, and 4 ml of 2.5 M n-BuLi was added dropwise. After stirring at -78 ° C for 1 hour, 2.59 g (10 mmol) of 2-bromo-9H-fluoren-9-one dissolved in 30 ml of THF was slowly added dropwise and the temperature was raised to room temperature to complete the reaction. MC and 2N HCl The organic layer was extracted.

무수 MgSO4로 유기층 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 화합물을 Hex : EA = 5 : 1로 컬럼하여 중간체 4 3.06g(79%)을 얻었다.Water in the organic layer was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting compound was subjected to column chromatography with Hex: EA = 5: 1 to obtain 3.06 g (79%) of Intermediate 4.

상기 화합물-1를 아세트산에 녹인 후 진한 염산을 첨가하고 1시간 환류하여 반응을 완결하였다. 에테르와 물을 사용하여 추출한 후 유기층을 포화된 NaHCO3으로 씻어주었다. 유기층을 MgSO4로 건조한 후 재결정 및 Hex : EA = 5 : 1로 컬럼하여 화합물 6 2.99g(81%)을 얻었다.Compound-1 was dissolved in acetic acid, concentrated hydrochloric acid was added, and the mixture was refluxed for 1 hour to complete the reaction. After extracting with ether and water, the organic layer was washed with saturated NaHCO 3 . The organic layer was dried over MgSO 4 , recrystallized and columned with Hex: EA = 5: 1 to obtain 2.99 g (81%) of Compound 6. [

중간체 4 MS(FAB): 387(M+)Intermediate 4 MS (FAB): 387 (M &lt; + & gt ; ) [

화합물 6 MS(FAB): 369(M+)Compound 6 MS (FAB): 369 (M &lt; + & gt ; ).

화합물 7의 합성Synthesis of Compound 7

[반응식 8][Reaction Scheme 8]

Figure 112016073236473-pat00025
Figure 112016073236473-pat00025

3-브로모-1-요오도나프탈렌 3.33g(10mmol)을 THF 15ml에 녹인 후 -78℃로 낮추고 2.5M n-BuLi 4ml를 적가하였다. -78℃에서 1시간 교반 후 THF 30ml에 녹인 9H-플루오렌-9-온 1.80g(10mmol)을 천천히 적가하고 상온으로 승온하여 반응을 완결한 후 MC와 2N HCl을 첨가하고 유기층을 추출하였다.3.33 g (10 mmol) of 3-bromo-1-iodonaphthalene was dissolved in 15 ml of THF, then cooled to -78 ° C, and 4 ml of 2.5 M n-BuLi was added dropwise. After stirring at -78 ° C for 1 hour, 1.80 g (10 mmol) of 9H-fluorene-9-one dissolved in 30 ml of THF was slowly added dropwise and the temperature was raised to room temperature to complete the reaction. MC and 2N HCl were added and the organic layer was extracted.

무수 MgSO4로 유기층 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 화합물을 Hex : EA = 5 : 1로 컬럼하여 중간체 5 2.48g(64%)을 얻었다.Water in the organic layer was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting compound was subjected to column chromatography with Hex: EA = 5: 1 to obtain 2.48 g (64%) of Intermediate 5.

상기 중간체 5를 아세트산에 녹인 후 진한 염산을 첨가하고 1시간 환류하여 반응을 완결하였다. 에테르와 물을 사용하여 추출한 후 유기층을 포화된 NaHCO3으로 씻어주었다. 유기층을 MgSO4로 건조한 후 재결정 및 Hex : EA = 5 : 1로 컬럼하여 화합물 7 2.81g(76%)을 얻었다.The intermediate 5 was dissolved in acetic acid, concentrated hydrochloric acid was added, and the mixture was refluxed for 1 hour to complete the reaction. After extracting with ether and water, the organic layer was washed with saturated NaHCO 3 . The organic layer was dried over MgSO 4 , recrystallized, and then subjected to column chromatography with Hex: EA = 5: 1 to obtain 2.81 g (76%) of Compound 7.

중간체 5 MS(FAB): 387(M+)Intermediate 5 MS (FAB): 387 (M &lt; + & gt ; ) [

화합물 7 MS(FAB): 369(M+)Compound 7 MS (FAB): 369 (M <+> ) <

화합물 8의 합성Synthesis of Compound 8

[반응식 9][Reaction Scheme 9]

Figure 112016073236473-pat00026
Figure 112016073236473-pat00026

질소 하에서 화합물 6 3.69g(10mmol)을 무수 THF 40ml에 녹이고, 반응물의 온도를 -78℃로 낮추고, 2.5M n-BuLi 4ml를 천천히 적가하고 난 후, 반응물을 0℃에서 1시간동안 교반시켰다. 이후, 반응물의 온도를 -78℃로 낮추고 트리메틸보레이트 12.47g(12mmol)을 적가하고 난 후 상온에서 12시간동안 교반시켰다. 반응이 종결되면 2N-HCl 수용액을 넣고, 30분간 교반시킨 후 에테르로 추출하였다.Under nitrogen, 3.69 g (10 mmol) of compound 6 was dissolved in 40 ml of anhydrous THF, the temperature of the reaction was lowered to -78 ° C, 4 ml of 2.5M n-BuLi was slowly added dropwise and the reaction was stirred at 0 ° C for 1 hour. Then, the temperature of the reactant was lowered to -78 ° C, 12.47 g (12 mmol) of trimethylborate was added dropwise, and the mixture was stirred at room temperature for 12 hours. When the reaction was completed, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether.

무수 MgSO4로 유기층 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 화합물을 Hex : EA = 5 : 1로 컬럼하여 화합물 8 2.47g(74%)을 얻었다.Water in the organic layer was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting compound was subjected to column chromatography with Hex: EA = 5: 1 to obtain 2.47 g (74%) of Compound 8.

화합물 8 MS(FAB): 334(M+)Compound 8 MS (FAB): 334 (M <+> ) <

화합물 9의 합성Synthesis of Compound 9

[반응식 10][Reaction Scheme 10]

Figure 112016073236473-pat00027
Figure 112016073236473-pat00027

질소 하에서 화합물 8 3.34g(10mmol)과 1-브로모-3-요오도벤젠 2.83g(10mmol)을 주입하고 THF 40ml에 녹인 후, Pd(PPh3)4 0.58g(0.5mmol)과 2M K2CO3 15ml(30mmol)를 각각 넣은 다음 24시간 동안 환류시켰다.After the nitrogen compound in the 8 3.34g (10mmol) and 1-bromo-3-iodo-benzene injection 2.83g (10mmol) is dissolved in THF 40ml, Pd (PPh 3) 4 0.58g (0.5mmol) and 2M K 2 15 ml (30 mmol) of CO 3 were added, respectively, and the mixture was refluxed for 24 hours.

반응이 종료되면 반응물의 온도를 상온으로 식히고, MC 200ml, H2O 200ml를 첨가하여 MC층을 추출한 후 무수 MgSO4로 건조하고 농축한 후 Hex : EA = 5 : 1로 컬럼하여 화합물 9 3.25g(73%)을 얻었다.After the completion of the reaction, the reaction mixture was cooled to room temperature, 200 ml of MC and 200 ml of H 2 O were added to extract the MC layer. The MC layer was dried over anhydrous MgSO 4 and concentrated. The product was then subjected to column chromatography with Hex: EA = (73%).

1H NMR (DMSO, 300Hz): δ(ppm)= 8.07-7.66 (m, 4H), 7.64-7.23(m, 9H), 7.20-6.91(m, 2H), 6.89-6.60(d, 2H) 1 H NMR (DMSO, 300Hz) : δ (ppm) = 8.07-7.66 (m, 4H), 7.64-7.23 (m, 9H), 7.20-6.91 (m, 2H), 6.89-6.60 (d, 2H)

화합물 9 MS(FAB): 445(M+)Compound 9 MS (FAB): 445 (M &lt; + & gt ; ).

화합물 10의 합성Synthesis of Compound 10

[반응식 11][Reaction Scheme 11]

Figure 112016073236473-pat00028
Figure 112016073236473-pat00028

질소 하에서 화합물 6 3.34g(10mmol)과 1-브로모-4-요오도벤젠 2.83g(10mmol)을 주입하고 THF 40ml에 녹인 후, Pd(PPh3)4 0.58g(0.5mmol)과 2M K2CO3 15ml(30mmol)를 각각 넣은 다음 24시간 동안 환류시켰다.After the nitrogen compound in the 6 3.34g (10mmol) and 1-bromo-4-iodo benzene injection 2.83g (10mmol) is dissolved in THF 40ml, Pd (PPh 3) 4 0.58g (0.5mmol) and 2M K 2 15 ml (30 mmol) of CO 3 were added, respectively, and the mixture was refluxed for 24 hours.

반응이 종료되면 반응물의 온도를 상온으로 식히고, MC 200ml, H2O 200ml를 첨가하여 MC층을 추출한 후 무수 MgSO4로 건조하고 농축한 후 Hex : EA = 4 : 1로 컬럼하여 화합물 10 3.34g(75%)을 얻었다.After the completion of the reaction, the reaction mixture was cooled to room temperature, 200 ml of MC and 200 ml of H 2 O were added thereto to extract the MC layer. The MC layer was dried over anhydrous MgSO 4 and concentrated. A column of Hex: EA = 4: (75%).

1H NMR (DMSO, 300Hz): δ(ppm)= 8.07-7.66 (m, 4H), 7.64-7.25(m, 9H), 7.22-6.91(m, 2H), 6.87-6.60(d, 2H) 1 H NMR (DMSO, 300Hz) : δ (ppm) = 8.07-7.66 (m, 4H), 7.64-7.25 (m, 9H), 7.22-6.91 (m, 2H), 6.87-6.60 (d, 2H)

화합물 10 MS(FAB): 445(M+)Compound 10 MS (FAB): 445 (M &lt; + & gt ; ).

화합물 11의 합성Synthesis of Compound 11

[반응식 12][Reaction Scheme 12]

Figure 112016073236473-pat00029
Figure 112016073236473-pat00029

1-요오도나프탈렌 2.54g(10mmol)을 THF 15ml에 녹인 후 -78℃로 낮추고 2.5M n-BuLi 4ml를 적가하였다. -78℃에서 1시간 교반 후 THF 30ml에 녹인 2,7-디브로모-9H-플루오렌-9-온 3.38g(10mmol)을 천천히 적가하고 상온으로 승온하여 반응을 완결한 후 MC와 2N HCl을 첨가하고 유기층을 추출하였다.2.54 g (10 mmol) of 1-iodonaphthalene was dissolved in 15 ml of THF and then cooled to -78 ° C, and 4 ml of 2.5 M n-BuLi was added dropwise. After stirring at -78 ° C for 1 hour, 3.38 g (10 mmol) of 2,7-dibromo-9H-fluoren-9-one dissolved in 30 ml of THF was slowly added dropwise and the temperature was raised to room temperature to complete the reaction. Was added and the organic layer was extracted.

무수 MgSO4로 유기층 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 화합물을 Hex : EA = 3 : 1로 컬럼하여 중간체 6 3.31g(71%)을 얻었다.Water in the organic layer was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting compound was subjected to column chromatography with Hex: EA = 3: 1 to obtain 3.31 g (71%) of Intermediate 6. [

상기 화합물-8를 아세트산에 녹인 후 진한 염산을 첨가하고 1시간 환류하여 반응을 완결하였다. 에테르와 물을 사용하여 추출한 후 유기층을 포화된 NaHCO3으로 씻어주었다. 유기층을 MgSO4로 건조한 후 재결정 및 Hex : EA = 5 : 1로 컬럼하여 화합물 11 3.45g(77%)을 얻었다.Compound-8 was dissolved in acetic acid, concentrated hydrochloric acid was added, and the reaction was completed by refluxing for 1 hour. After extracting with ether and water, the organic layer was washed with saturated NaHCO 3 . The organic layer was dried over MgSO 4 and then recrystallized and columned at Hex: EA = 5: 1 to obtain 3.45 g (77%) of Compound 11.

중간체 6 MS(FAB): 466(M+)Intermediate 6 MS (FAB): 466 (M &lt; + & gt ; ) [

화합물 11 MS(FAB): 448(M+)Compound 11 MS (FAB): 448 (M &lt; + & gt ; ).

화합물 12의 합성Synthesis of Compound 12

[반응식 13][Reaction Scheme 13]

Figure 112016073236473-pat00030
Figure 112016073236473-pat00030

질소 하에서 화합물 11 4.48g(10mmol)과 페닐보론산 1.22g(10mmol)을 주입하고 THF 40ml에 녹인 후, Pd(PPh3)4 0.58g(0.5mmol), 2M K2CO3 15ml(30mmol)을 첨가하여 24시간 동안 환류하였다.After injection of the compound 11 4.48g (10mmol) and phenylboronic acid 1.22g (10mmol) under nitrogen and dissolved in THF 40ml, the Pd (PPh 3) 4 0.58g ( 0.5mmol), 2M K 2 CO 3 15ml (30mmol) And the mixture was refluxed for 24 hours.

반응 완결 후 MC 200ml, H2O 200ml를 첨가하여 MC층을 추출한 후 무수 MgSO4로 건조하고 농축한 후 Hex : EA = 4 : 1로 컬럼하여 화합물 12 3.16g(71%)을 얻었다.After the completion of the reaction, 200 ml of MC and 200 ml of H 2 O were added to extract the MC layer, followed by drying with anhydrous MgSO 4 , followed by concentration with Hex: EA = 4: 1 to obtain 3.16 g (71%) of Compound 12.

화합물 12 MS(FAB): 445(M+)Compound 12 MS (FAB): 445 (M &lt; + & gt ; ).

화합물 13의 합성Synthesis of Compound 13

[반응식 14][Reaction Scheme 14]

Figure 112016073236473-pat00031
Figure 112016073236473-pat00031

질소 하에서 화합물 12 4.45g(10mmol)을 무수 THF 40ml에 녹이고, 반응물의 온도를 -78℃로 낮추고, 2.5M n-BuLi 4ml를 천천히 적가하고 난 후, 반응물을 0℃에서 1시간동안 교반시켰다. 이후, 반응물의 온도를 -78℃로 낮추고 트리메틸보레이트 12.47g(12mmol)을 적가하고 난 후 상온에서 12시간동안 교반시켰다. 반응이 종결되면 2N-HCl 수용액을 넣고, 30분간 교반시킨 후 에테르로 추출하였다.Under nitrogen, 4.45 g (10 mmol) of compound 12 was dissolved in 40 ml of anhydrous THF, the temperature of the reaction was lowered to -78 ° C, 4 ml of 2.5 M n-BuLi was slowly added dropwise and the reaction was stirred at 0 ° C for 1 hour. Then, the temperature of the reactant was lowered to -78 ° C, 12.47 g (12 mmol) of trimethylborate was added dropwise, and the mixture was stirred at room temperature for 12 hours. When the reaction was completed, 2N-HCl aqueous solution was added, stirred for 30 minutes, and extracted with ether.

무수 MgSO4로 유기층 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 화합물을 Hex : EA = 4 : 1로 컬럼하여 화합물 13 3.04g(74%)을 얻었다.Water in the organic layer was removed with anhydrous MgSO 4 , filtered under reduced pressure, and the organic solvent was concentrated. The resulting compound was subjected to column chromatography with Hex: EA = 4: 1 to obtain 3.04 g (74%) of Compound 13.

화합물 13 MS(FAB): 410(M+)Compound 13 MS (FAB): 410 (M &lt; + & gt ; ).

화합물 14의 합성Synthesis of Compound 14

[반응식 15][Reaction Scheme 15]

Figure 112016073236473-pat00032
Figure 112016073236473-pat00032

질소 하에서 화합물 13 4.10g(10mmol)과 1-브로모-3-요오도벤젠 2.83g(10mmol)을 주입하고 THF 40ml에 녹인 후, Pd(PPh3)4 0.58g(0.5mmol)과 2M K2CO3 15ml(30mmol)를 각각 넣은 다음 24시간 동안 환류시켰다.After a nitrogen compound 13 4.10g (10mmol) and 1-bromo-3-iodo-benzene injection 2.83g (10mmol) is dissolved in THF 40ml, Pd (PPh 3) 4 0.58g (0.5mmol) and 2M K 2 15 ml (30 mmol) of CO 3 were added, respectively, and the mixture was refluxed for 24 hours.

반응이 종료되면 반응물의 온도를 상온으로 식히고, MC 200ml, H2O 200ml를 첨가하여 MC층을 추출한 후 무수 MgSO4로 건조하고 농축한 후 Hex : EA = 4 : 1로 컬럼하여 화합물 14 3.81g(73%)을 얻었다.After the completion of the reaction, the reaction mixture was cooled to room temperature, 200 ml of MC and 200 ml of H 2 O were added thereto to extract the MC layer. The MC layer was dried over anhydrous MgSO 4 , concentrated and then subjected to column chromatography with Hex: EA = 4: (73%).

1H NMR (DMSO, 300Hz): δ(ppm)= 8.10-7.78 (m, 4H), 7.76-7.25(m, 13H), 7.22-6.90(m, 2H), 6.87-6.60(d, 2H) 1 H NMR (DMSO, 300Hz) : δ (ppm) = 8.10-7.78 (m, 4H), 7.76-7.25 (m, 13H), 7.22-6.90 (m, 2H), 6.87-6.60 (d, 2H)

화합물 14 MS(FAB): 521(M+)Compound 14 MS (FAB): 521 (M &lt; + & gt ; ).

중간체 7의 합성Synthesis of Intermediate 7

[반응식 16][Reaction Scheme 16]

Figure 112016073236473-pat00033
Figure 112016073236473-pat00033

질소 하에서 4-브로모피리딘 1.58g(10mmol)과 아닐린 2.79g(30mmol)을 톨루엔 40ml에 녹인 후 t-BuONa 2.88g(30mmol), Pd(OAc)2 45mg(0.2mmol), BINAP 0.25g(0.4mmol)을 첨가하여 2시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, MC 150ml, H2O 150ml를 첨가하여 MC층을 추출한 후 무수 MgSO4로 건조하고 농축한 후 Hex : EA = 4 : 1로 컬럼하여 중간체 7 1.24g(73%)을 얻었다.(30 mmol) of t-BuONa, 45 mg (0.2 mmol) of Pd (OAc) 2 and 0.25 g (0.4 mmol) of BINAP were added to a solution of 1.58 g (10 mmole) of 4-bromopyridine and 2.79 g mmol) was added and the mixture was refluxed for 2 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature, 150 ml of MC and 150 ml of H 2 O were added thereto. The MC layer was extracted, dried over anhydrous MgSO 4 and concentrated. The product thus obtained was subjected to column chromatography with Hex: EA = (73%).

중간체 7 MS(FAB): 170(M+)Intermediate 7 MS (FAB): 170 (M &lt; + & gt ; ) [

화합물 15의 합성Synthesis of Compound (15)

[반응식 17][Reaction Scheme 17]

Figure 112016073236473-pat00034
Figure 112016073236473-pat00034

질소 하에서 화합물 2 3.43g(10mmol)과 중간체 7 1.70g(10mmol)을 톨루엔 50ml에 녹인 후 Pd2dba3 0.18g(0.2mmol), t-Bu3P 0.4ml(0.4mmol), t-BuONa 2.88g(30mmol)을 첨가 후 12시간 동안 환류하였다.(10 mmol) of Compound 2 and 1.70 g (10 mmol) of Intermediate 7 were dissolved in 50 ml of toluene under nitrogen and then 0.18 g (0.2 mmol) of Pd 2 dba 3 , 0.4 ml (0.4 mmol) of t-Bu 3 P, g (30 mmol) was added and the mixture was refluxed for 12 hours.

반응 완결 후 MC 250ml, H2O 250ml를 첨가하여 MC층을 추출하고, 유기층을 감압증류 후 Hex : MC = 2 : 1로 컬럼하여 화합물 15 3.29g(76%)을 얻었다.After completion of the reaction, 250 ml of MC and 250 ml of H 2 O were added to extract the MC layer. The organic layer was distilled under reduced pressure and then subjected to column chromatography with Hex: MC = 2: 1 to obtain 3.29 g (76%) of Compound 15.

1H NMR (DMSO, 300Hz): δ(ppm)= 8.55-8.25(d, 2H), 8.21-8.10 (m, 1 H), 8.10-7.80(m, 2 H), 7.75-6.90(m, 11H), 6.90-6.55(m, 4H) 1 H NMR (DMSO, 300 Hz): [delta] (ppm) = 8.55-8.25 (d, 2H), 8.21-8.10 (m, 1H), 8.10-7.80 (m, 2H), 7.75-6.90 ), 6.90 - 6.55 (m, 4H)

화합물 15 MS(FAB): 432(M+)Compound 15 MS (FAB): 432 (M &lt; + & gt ; ).

화합물 16의 합성Synthesis of Compound 16

[반응식 18][Reaction Scheme 18]

Figure 112016073236473-pat00035
Figure 112016073236473-pat00035

질소 하에서 화합물 6 3.69g(10mmol)과 중간체 7 1.70g(10mmol)을 톨루엔 50ml에 녹인 후 Pd2dba3 0.18g(0.2mmol), t-Bu3P 0.4ml(0.4mmol), t-BuONa 2.88g(30mmol)을 첨가 후 12시간 동안 환류하였다.(10 mmol) of Compound 6 and 1.70 g (10 mmol) of Intermediate 7 were dissolved in 50 ml of toluene under nitrogen and then 0.18 g (0.2 mmol) of Pd 2 dba 3 , 0.4 ml (0.4 mmol) of t-Bu 3 P, g (30 mmol) was added and the mixture was refluxed for 12 hours.

반응 완결 후 MC 250ml, H2O 250ml를 첨가하여 MC층을 추출하고, 유기층을 감압증류 후 Hex : MC = 2 : 1로 컬럼하여 화합물 16 3.58g(78%)을 얻었다.After completion of the reaction, 250 ml of MC and 250 ml of H 2 O were added to extract the MC layer. The organic layer was distilled under reduced pressure and then subjected to column chromatography with Hex: MC = 2: 1 to obtain 3.58 g (78%) of Compound 16.

1H NMR (DMSO, 300Hz): δ(ppm)= 8.57-8.25(d, 2H), 8.21-8.10 (m, 1 H), 8.10-7.75(m, 2 H), 7.72-6.90(m, 13H), 6.90-6.52(m, 4H) 1 H NMR (DMSO, 300 Hz): [delta] (ppm) = 8.57-8.25 (d, 2H), 8.21-8.10 (m, 1H), 8.10-7.75 (m, 2H), 7.72-6.90 ), 6.90-6.52 (m, 4H)

화합물 16 MS(FAB): 458(M+)Compound 16 MS (FAB): 458 (M &lt; + & gt ; ).

이하에서, 실시예를 통하여 본 발명을 보다 상세히 설명한다. 그러나, 하기의 실시예는 본 발명을 더욱 구체적으로 설명하기 위한 것으로서, 본 발명의 범위가 하기의 실시예에 의하여 한정되는 것은 아니다. 하기의 실시예는 본 발명의 범위 내에서 당업자에 의해 적절히 수정, 변경될 수 있다.Hereinafter, the present invention will be described in more detail by way of examples. However, the following examples are intended to further illustrate the present invention, and the scope of the present invention is not limited by the following examples. The following examples can be appropriately modified and changed by those skilled in the art within the scope of the present invention.

실시예Example 1. One.

애노드로서 15Ω/cm2 (1200Å) ITO 유리 기판을 45mm x 45mm x 0.7mm 크기로 잘라서 이소프로필 알코올과 순수를 이용하여 각 5분 동안 초음파 세정한 후, 30분 동안 자외선을 조사하고 오존에 노출시켜 세정하고 진공증착장치에 이 유리기판을 설치하였다.An ITO glass substrate of 15 Ω / cm 2 (1200 Å) as an anode was cut into a size of 45 mm × 45 mm × 0.7 mm, ultrasonically washed with isopropyl alcohol and pure water for 5 minutes, exposed to ultraviolet rays for 30 minutes and exposed to ozone And the glass substrate was placed in a vacuum vapor deposition apparatus.

상기 ITO층 상부에 하기 Ex-1로 표시된 CuPC를 약 300Å, 하기 Ex-2로 표시된 NPD(4,4'-bis[N-(1-naphtyl)-N-phenylamino]-biphenyl)를 약 900Å, 하기 Ex-3으로 표시된 DPBVi에 하기 Ex-4로 표시된 물질을 도펀트로 약 1% 첨가하여 약 200Å, 전자수송층으로 본 발명의 화합물 15를 약 350Å, LiF를 약 10Å, 알루미늄(Al)을 약 1000Å의 두께로 순차 적층하였다.(NPD) (4,4'-bis [N- (1-naphthyl) -N-phenylamino] -biphenyl] represented by the following Ex-2 was deposited to a thickness of about 900 Å on the ITO layer, The DPBVi represented by Ex-3 shown below was doped with about 1% by weight of a substance represented by Ex-4 shown below as a dopant to form an electron transport layer of about 350 Å, LiF about 10 Å, aluminum (Al) As shown in FIG.

실시예Example 2 2

상기 실시예 1에서 전자수송층으로 본 발명의 화합물 15대신 화합물 16을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 실시하여 유기 전계발광 소자를 제조하였다.An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Compound 16 was used instead of Compound 15 of the present invention as an electron transporting layer in Example 1.

비교예Comparative Example 1 One

상기 실시예 1에서 전자수송층으로 하기 Ex-5로 표시된 Alq3을 사용한 것을 제외하고는 상기 실시예 1과 동일하게 실시하여 유기 전계발광 소자를 제조하였다.An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Alq 3 represented by Ex-5 below was used as the electron transporting layer in Example 1.

Figure 112016073236473-pat00036
Figure 112016073236473-pat00036

시험예Test Example :  : 유기전계발광소자의The organic electroluminescent device 특성 평가 Character rating

상기 실시예에서 제조한 유기전계발광 소자 1, 2 및 비교예 1에서 제조한 유기 전계발광 소자의 특성을 전류 밀도 10mA/cm2에서 측정하였으며, 결과를 하기 표 1에 나타내었다.The characteristics of the organic electroluminescent devices 1 and 2 and the organic electroluminescent device prepared in Comparative Example 1 were measured at a current density of 10 mA / cm 2. The results are shown in Table 1 below.

Material Name Material Name Current Density
(mA/cm2) Current Density
(mA / cm 2 ) Voltage
(V) Voltage
(V) Efficiency
(Cd/A) Efficiency
(Cd / A) CIE (X Y) CIE (X Y) 비교예 1Comparative Example 1 Alq3 Alq 3 1010 5.25.2 4.104.10 (0.137 0.189)(0.137 0.189) 실시예 1Example 1 화합물-15Compound-15 1010 4.84.8 5.715.71 (0.136 0.187)(0.136 0.187) 실시예 2Example 2 화합물-16Compound-16 1010 4.94.9 5.535.53 (0.136 0.189)(0.136 0.189)

상기 표 1에서 알 수 있는 바와 같이, 본 발명의 실시예 1 및 2에 유기전계발광소자의 경우, 비교예 1의 유기전계발광소자와 비교하여 발광효율이 크게 개선됨을 확인할 수 있다. As can be seen from the above Table 1, in the organic electroluminescent device according to the first and second embodiments of the present invention, the luminous efficiency is greatly improved as compared with the organic electroluminescent device of the first comparative example.

상기 시험결과로부터 본 발명의 유기화합물은 전자수송물질로 사용되는 경우, 유기전계발광소자의 발광효율을 향상시키는 것을 알 수 있다. 그러므로, 본 발명의 유기화합물은 소자의 저전력구동을 가능하게 하여 소비전력을 감소시키는 효과도 제공할 수 있다. 또한, 저전력구동에 의해 유기전계발광소자의 발광수명도 향상시킬 수 있다. From the test results, it can be seen that the organic compound of the present invention improves the luminous efficiency of the organic electroluminescent device when it is used as an electron transporting material. Therefore, the organic compound of the present invention enables low power driving of the device, and can also provide an effect of reducing power consumption. Further, the light emission lifetime of the organic electroluminescent device can be improved by low-power driving.

Claims (8)

하기 화학식1로 표시되는 유기화합물:
[ 화학식1 ]
Figure 112016073236473-pat00037

상기 식에서
CYCLO는 탄소 4개 또는 5개로 이루어지는 고리이며,
상기 CYCLO가 탄소 4개로 이루어지는 고리인 경우 CYCLO를 형성하는 2개의 페닐기는 결합되어 나프탈렌기를 형성하며,
R1, R2, R3, R4, R5, R6, R7 및 R8은 각각 독립적으로 수소, 중수소, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 또는 탄소수 3 내지 40의 시클로 알킬기이거나,
F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~60의 방향족 탄화수소기이거나,
F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 60의 헤테로 방향족 탄화수소기이거나,
F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 및 탄소수 3 내지 40의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이다.An organic compound represented by the following formula (1):
[ Chemical Formula 1 ]
Figure 112016073236473-pat00037

In the above formula
CYCLO is a ring consisting of four or five carbons,
When the CYCLO is a ring having four carbon atoms, two phenyl groups forming CYCLO are bonded to form a naphthalene group,
R1, R2, R3, R4, R5, R6, R7 and R8 are each independently hydrogen, deuterium, F, Cl, Br, I , CN, Si (CH 3) 3, B (OH) 2, having 1 to 40 carbon atoms Straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, thioalkyl of 1 to 40 carbon atoms, or cycloalkyl group of 3 to 40 carbon atoms,
F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain or branched-chain C 1 -C 40 alkyl, thio C 1 -C 40 alkoxy, C 1 to 40 alkyl carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, dibenzofuranyl, dibenzofuranyl, An aromatic hydrocarbon group having 6 to 60 carbon atoms which is substituted or unsubstituted with at least one member selected from the group consisting of pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl groups,
F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain or branched-chain C 1 -C 40 alkyl, thio C 1 -C 40 alkoxy, C 1 to 40 alkyl carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, dibenzofuranyl, dibenzofuranyl, At least one element selected from the group consisting of S, O, N and Si, which is substituted or unsubstituted with at least one member selected from the group consisting of pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl and quinolinyl groups Or a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms,
F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain having 1 to 40 carbon atoms or branched chain alkyl, thioalkyl having 1 to 40 carbon atoms alkoxy having 1 to 40, and Anthracenyl, phenanthrenyl, pyrenyl substituted with phenyl, biphenyl, naphthyl, anthracenyl, phenyl groups substituted or unsubstituted with at least one member selected from the group consisting of a cycloalkyl group having 3 to 40 carbon atoms, An amino group substituted by at least one member selected from the group consisting of dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups. 청구항 1에 있어서,
상기 화학식 1은 하기 화학식 2 또는 화학식 3으로 표시되는 것을 특징으로 하는 유기화합물:
[ 화학식2 ]
Figure 112016073236473-pat00038

[ 화학식3 ]
Figure 112016073236473-pat00039

상기 식에서
R1, R2, R3, R4, R5, R6, R7 및 R8은 각각 독립적으로 수소, 중수소, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 또는 탄소수 3 내지 40의 시클로 알킬기이거나,
F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 탄소수 6~60의 방향족 탄화수소기이거나,
F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 탄소수 3 내지 40의 시클로 알킬, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환되고, S, O, N 및 Si로 이루어진 군으로부터 선택되는 하나 이상의 원소를 포함하는 탄소수 5 내지 60의 헤테로 방향족 탄화수소기이거나,
F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, 탄소수 1 내지 40의 직쇄 또는 분지쇄 알킬, 탄소수 1 내지 40의 알콕시, 탄소수 1 내지 40의 티오알킬, 및 탄소수 3 내지 40의 시클로 알킬기로 이루어진 군으로부터 선택되는 1종 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 및 피리미디닐기로 이루어진 군으로부터 선택되는 1종 이상으로 치환된 아미노기이다.The method according to claim 1,
The organic compound represented by Formula 1 is represented by Formula 2 or Formula 3:
[Formula 2]
Figure 112016073236473-pat00038

[Formula 3]
Figure 112016073236473-pat00039

In the above formula
R1, R2, R3, R4, R5, R6, R7 and R8 are each independently hydrogen, deuterium, F, Cl, Br, I , CN, Si (CH 3) 3, B (OH) 2, having 1 to 40 carbon atoms Straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, thioalkyl of 1 to 40 carbon atoms, or cycloalkyl group of 3 to 40 carbon atoms,
F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain or branched-chain C 1 -C 40 alkyl, thio C 1 -C 40 alkoxy, C 1 to 40 alkyl carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, dibenzofuranyl, dibenzofuranyl, An aromatic hydrocarbon group having 6 to 60 carbon atoms which is substituted or unsubstituted with at least one member selected from the group consisting of pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl groups,
F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain or branched-chain C 1 -C 40 alkyl, thio C 1 -C 40 alkoxy, C 1 to 40 alkyl carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, dibenzofuranyl, dibenzofuranyl, At least one element selected from the group consisting of S, O, N and Si, which is substituted or unsubstituted with at least one member selected from the group consisting of pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl and quinolinyl groups Or a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms,
F, Cl, Br, I, CN, Si (CH 3) 3, B (OH) 2, a straight-chain having 1 to 40 carbon atoms or branched chain alkyl, thioalkyl having 1 to 40 carbon atoms alkoxy having 1 to 40, and Anthracenyl, phenanthrenyl, pyrenyl substituted with phenyl, biphenyl, naphthyl, anthracenyl, phenyl group substituted or unsubstituted with at least one member selected from the group consisting of a cycloalkyl group having 3 to 40 carbon atoms, An amino group substituted by at least one member selected from the group consisting of dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups. 청구항 2에 있어서,
R1, R2, R3, R4, R5, R6, R7 및 R8은 각각 독립적으로 수소, 중수소, F, Cl, Br, I, B(OH)2, 또는 탄소수 1 내지 10의 직쇄 또는 분지쇄 알킬기이거나,
F, Cl, Br, I, B(OH)2, 및 탄소수 1 내지 10의 직쇄 또는 분지쇄 알킬기, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 및 퀴놀리닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 안트라세닐, 페난트렌일, 파이레닐기이거나,
F, Cl, Br, I, B(OH)2, 및 탄소수 1 내지 10의 직쇄 또는 분지쇄 알킬기, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 디벤조퓨란일, 피롤, 트리아졸, 피리딘일, 피라지닐, 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상으로 치환 또는 비치환된 피롤, 트리아졸, 피리딘일, 피라지닐, 피리미디닐기, 퀴놀리닐기, 9,9-디메틸플루오레닐, 카르바졸일, 또는 디벤조퓨란일기이거나,
F, Cl, Br, I, B(OH)2, 및 탄소수 1 내지 10의 직쇄 또는 분지쇄 알킬기, 페닐, 바이페닐, 나프틸, 안트라세닐, 페닐기로 치환된 안트라세닐, 페난트렌일, 파이레닐, 9,9-디메틸플루오레닐, 카르바졸일, 퀴놀리닐, 및 디벤조퓨란일기로 이루어진 군으로부터 선택되는 하나 이상으로 치환된 아미노기이다.The method of claim 2,
Wherein R 1, R 2, R 3, R 4, R 5, R 6, R 7 and R 8 are each independently selected from the group consisting of hydrogen, deuterium, F, Cl, Br, I, B (OH) 2 or a straight or branched alkyl group having 1 to 10 carbon atoms,
(I) wherein R 1 and R 2 are each independently selected from the group consisting of F, Cl, Br, I, B (OH) 2 and straight or branched chain alkyl groups having 1 to 10 carbon atoms, anthracenyl, phenanthrenyl, pyrenyl substituted with phenyl, biphenyl, naphthyl, anthracenyl, , Pyridyl, pyridinyl, pyrimidinyl, quinolinyl, and quinolinyl groups, each of which is optionally substituted with one or more substituents selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, A substituted or unsubstituted phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl,
(I) wherein R 1 and R 2 are each independently selected from the group consisting of F, Cl, Br, I, B (OH) 2 and straight or branched chain alkyl groups having 1 to 10 carbon atoms, anthracenyl, phenanthrenyl, pyrenyl substituted with phenyl, biphenyl, naphthyl, anthracenyl, Substituted or unsubstituted pyrroles selected from the group consisting of pyrrolidinyl, pyrrolidinyl, pyrrolidinyl, pyrrolidinyl, pyrrolidinyl, pyrrolidinyl, pyrrolidinyl, Triazol, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, 9,9-dimethylfluorenyl, carbazolyl, or dibenzofuranyl group,
(I) wherein R 1 and R 2 are each independently selected from the group consisting of F, Cl, Br, I, B (OH) 2 and straight or branched chain alkyl groups having 1 to 10 carbon atoms, anthracenyl, phenanthrenyl, pyrenyl substituted with phenyl, biphenyl, naphthyl, anthracenyl, , 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, and dibenzofuranyl groups. 청구항 2에 있어서,
상기 화학식 2 또는 화학식 3으로 표시되는 화합물은 하기 화학식의 화합물 1 내지 48 중의 어느 하나인 것을 특징으로 하는 유기화합물:
Figure 112016073236473-pat00040

Figure 112016073236473-pat00041

Figure 112016073236473-pat00042

Figure 112016073236473-pat00043

Figure 112016073236473-pat00044

Figure 112016073236473-pat00045

Figure 112016073236473-pat00046

Figure 112016073236473-pat00047

Figure 112016073236473-pat00048

Figure 112016073236473-pat00049

Figure 112016073236473-pat00050

Figure 112016073236473-pat00051

Figure 112016073236473-pat00052
The method of claim 2,
Wherein the compound represented by Formula 2 or Formula 3 is any one of Compounds 1 to 48 represented by the following formulas:
Figure 112016073236473-pat00040

Figure 112016073236473-pat00041

Figure 112016073236473-pat00042

Figure 112016073236473-pat00043

Figure 112016073236473-pat00044

Figure 112016073236473-pat00045

Figure 112016073236473-pat00046

Figure 112016073236473-pat00047

Figure 112016073236473-pat00048

Figure 112016073236473-pat00049

Figure 112016073236473-pat00050

Figure 112016073236473-pat00051

Figure 112016073236473-pat00052
 청구항 1에 있어서,
상기 유기화합물은 전자재료용, 정밀화학용, 또는 의약용으로 사용되는 것을 특징으로 하는 유기화합물.The method according to claim 1,
The organic compound is used for an electronic material, a fine chemical, or a medicine. 청구항 1에 있어서,
상기 유기화합물은 유기전계발광소자용 재료 중 정공주입층 물질, 정공수송층 물질, 전자차단층 물질, 발광층 물질, 전자수송층 물질 또는 전자주입층 물질로 사용되는 것을 특징으로 하는 유기화합물.The method according to claim 1,
Wherein the organic compound is used as a hole injecting layer material, a hole transporting layer material, an electron blocking layer material, a light emitting layer material, an electron transporting layer material, or an electron injecting layer material in the material for an organic electroluminescence device. 음극과 양극사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기박막층이 협지되어있는 유기전기발광소자에 있어서,
상기 유기박막층중 적어도 1층 이상이 청구항 1의 유기화합물을 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기전기발광소자.An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,
Wherein at least one of the organic thin film layers contains the organic compound of claim 1 singly or in combination of two or more kinds. 청구항 7항에 있어서,
상기 유기전기발광소자가 양극, 정공주입층, 정공수송층, 전자차단층, 발광층, 전자수송층, 전자주입층 및 음극이 이 순서대로 적층된 구조를 갖는 것을 특징으로 하는 유기전기발광소자.The method of claim 7,
Wherein the organic electroluminescent device has a structure in which an anode, a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode are stacked in this order.
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